Methyl iodide → HCID 20272630, compound

HRID 371368

Reaction equation

HRID 371368 reaction equation
[CH2:1]([Mg]Cl)C(C)C.C(Cl)C(C)C.[Mg].[F:13][C:14]([F:26])([F:25])[CH:15]([OH:24])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CI>CCOCC.[CH-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.Cl[Ti]Cl>[F:13][C:14]([F:25])([F:26])[CH:15]([OH:24])/[CH:16]=[C:17](\[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)/[CH3:1]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 10554Isobutyl chlorideHCID 5462224MagnesiumHCID 114129783-Butyn-2-ol, 1,1,1-trifluoro-4-phenyl-HCID 178418368HCID 178418368, compound

Product 1

HCID 20272630HCID 20272630, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 416358Bis(cyclopentadienyl)titanium(IV) chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

In an isobutylmagnesium chloride solution that was prepared by reacting isobutyl chloride (3.74 g, 40 mmol) and magnesium (0.97 g, 40 mmol) in dry ether (40 ml) at 0° C., dichlorobis(π-cyclopentadienyl)titanium (0.22 g, 0.9 mmol) and 1,1,1-trifluoro-4-phenyl-3-butyne-2-ol (2 g, 10 mmol) were slowly added at 0° C. After 4 hour agitation of the mixture at room temperature, solvent was removed under heating for 30 min. Next, dry tetrahydrofuran (20 ml) was put into the reaction vessel and further methyl iodide (12.7 g, 90 mmol) was slowly added. After 12 hour agitation, the reaction mixture was treated by a method similar to the one in the above Examples to obtain (Z)-1,1,1-trifluoro-4-phenyl-3-pentene-2-ol (b.p.: 84°-86° C./2 mmHg) at a yield of 63%. The above product gave the following analytical data:

Workup

  1. customat 0° C.
  2. customsolvent was removed
  3. temperatureunder heating for 30 min
  4. additionwas slowly added
  5. waitAfter 12 hour agitation

Sources & evidence

ORD record
ord-c7b863e996644d2aa218b8222f6844f3
Source dataset
uspto-grants-1985_07
Patent number
US04532020

Linked notes

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